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WO2005047264A1 - Procede de production de zwitterions de dihydroisoquinoline - Google Patents

Procede de production de zwitterions de dihydroisoquinoline Download PDF

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Publication number
WO2005047264A1
WO2005047264A1 PCT/US2004/036987 US2004036987W WO2005047264A1 WO 2005047264 A1 WO2005047264 A1 WO 2005047264A1 US 2004036987 W US2004036987 W US 2004036987W WO 2005047264 A1 WO2005047264 A1 WO 2005047264A1
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WO
WIPO (PCT)
Prior art keywords
substituted
sulfur trioxide
dihydroisoquinoline
unsubstituted
reaction
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2004/036987
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English (en)
Inventor
George Douglas Ii Hiler
George Scot Miracle
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Procter and Gamble Co
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Procter and Gamble Co
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Filing date
Publication date
Application filed by Procter and Gamble Co filed Critical Procter and Gamble Co
Priority to JP2006538520A priority Critical patent/JP2007513071A/ja
Priority to CA002544547A priority patent/CA2544547A1/fr
Priority to EP04800814A priority patent/EP1680404A1/fr
Priority to MXPA06005028A priority patent/MXPA06005028A/es
Publication of WO2005047264A1 publication Critical patent/WO2005047264A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
    • C07D217/10—Quaternary compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
    • C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/39—Organic or inorganic per-compounds
    • C11D3/3902—Organic or inorganic per-compounds combined with specific additives
    • C11D3/3905—Bleach activators or bleach catalysts
    • C11D3/3907—Organic compounds
    • C11D3/3917—Nitrogen-containing compounds

Definitions

  • This invention relates to processes for producing molecules useful as organic catalysts, organic catalysts, cleaning compositions comprising such catalysts, and methods of using such catalysts and cleaning products.
  • Oxygen bleaching agents for example hydrogen peroxide
  • Oxygen bleaching agents are typically used to bleach fibers and various surfaces.
  • Unfortunately such agents are extremely temperature rate dependent.
  • the bleaching action of such solutions is markedly decreased.
  • certain organic catalysts have been developed. As the processes of preparing such catalysts are generally complex, such processes are time consuming and expensive. ' Accordingly, there is a need for an efficient and effective process of making an organic catalyst that provides the low temperature performance that industry and the consumer demands.
  • the present invention relates to a process of making an organic catalyst comprising the step of reacting a substituted or unsubstituted 3,4-dihydroisoquinoline sulfur trioxide complex with a substituted or unsubstituted epoxide to form said organic catalyst, or reacting a substituted or unsubstituted 3,4-dihydroisoquinoline with a substituted or unsubstituted epoxide sulfur trioxide complex to form said organic catalyst.
  • the present invention also relates to organic catalysts, cleaning compositions comprising said organic catalysts, and methods of using such organic catalysts and cleaning compositions.
  • cleaning composition includes, unless otherwise indicated, granular or powder-form all-purpose or "heavy-duty” washing agents, especially laundry detergents; liquid, gel or paste-form all-purpose washing agents, especially the so-called heavy- duty liquid types; liquid fine-fabric detergents; hand dishwashing agents or light duty dishwashing agents, especially those of the high-foaming type; machine dishwashing agents, including the various tablet, granular, liquid and rinse-aid types for household and institutional use; liquid cleaning and disinfecting agents, including antibacterial hand-wash types, laundry bars, mouthwashes, denture cleaners, car or carpet shampoos, bathroom cleaners; hair shampoos and hair-rinses; shower gels and foam baths and metal cleaners; as well as cleaning auxiliaries such as bleach additives and "stain-stick" or pre-treat types.
  • R groups may be: AAA, BBB, CCC, AAB, AAC, BBA, BBC, CCA, CCB, ABC.
  • substituted means that the organic composition or radical to which the term is applied is: (a) made unsaturated by the elimination of elements or radical; or (b) at least one hydrogen in the compound or radical is replaced with a moiety containing one or more (i) carbon, (ii) oxygen, (iii) sulfur, (iv) nitrogen or (v) halogen atoms; or (c) both (a) and (b).
  • Moieties which may replace hydrogen as described in (b) immediately above, that contain only carbon and hydrogen atoms are hydrocarbon moieties including, but not limited to, alkyl, alkenyl, alkynyl, alkyldienyl, cycloalkyl, phenyl, alkyl phenyl, naphthyl, anthryl, phenanthryl, fluoryl, steroid groups, and combinations of these groups with each other and with polyvalent hydrocarbon groups such as alkylene, alkylidene and alkylidyne groups.
  • Moieties containing oxygen atoms that may replace hydrogen as described in (b) immediately above include, but are not limited to, hydroxy, acyl or keto, ether, epoxy, carboxy, and ester containing groups.
  • Moieties containing sulfur atoms that may replace hydrogen as described in (b) immediately above include, but are not limited to, the sulfur-containing acids and acid ester groups, thioether groups, mercapto groups and thioketo groups.
  • Moieties containing nitrogen atoms that may replace hydrogen as described in (b) immediately above include, but are not limited to, amino groups, the nitro group, azo groups, ammonium groups, amide groups, azido groups, isocyanate groups, cyano groups and nitrile groups.
  • Moieties containing halogen atoms that may replace hydrogen as described in (b) immediately above include chloro, bromo, fluoro, iodo groups and any of the moieties previously described where a hydrogen or a pendant alkyl group is substituted by a halo group to form a stable substituted moiety. It is understood that any of the above moieties (b)(i) through (b)(v) can be substituted into each other in either a monovalent substitution or by loss of hydrogen in a polyvalent substitution to form another monovalent moiety that can replace hydrogen in the organic compound or radical.
  • the articles a and an when used in a claim are understood to mean one or more of the material that is claimed or described.
  • Ri is a aryl or heteroaryl group that can be substituted or unsubstituted
  • R 2 is a substituted or unsubstituted alkyl
  • R is a Ci to C 2 o substituted alkyl
  • R 5 is the moiety -CR ⁇ Ri 2 -X-G b -X c -[(CR 9 R ⁇ o)y-O] k -R 8 wherein: each X is independently selected from the group consisting of O, S, N-H, orN-R 8 ; and each R 8 is independently selected from the group
  • such catalyst molecule has Formula 1 above: wherein: Ri is a aryl or heteroaryl group that can be substituted or unsubstituted; R 2 is a substituted or unsubstituted alkyl; Ri and R when taken together with the iminium form a six membered ring; R 3 is a substituted C 2 alkyl; Rt is OSO 3 " ; R 5 is the moiety -CH 2 -O-R 8 wherein R 8 is independently selected from the group consisting of alkyl, aryl and heteroaryl, said R 8 moiety being substituted or unsubstituted, and whether substituted or unsubsituted said R 8 moiety having less than 21 carbons; and Rs is H, or an alkyl, aryl or heteroaryl moiety; said moieties being substituted or unsubstituted.
  • the process of making the aforementioned catalyst comprises the step of reacting a substituted or unsubstituted 3,4-dihydroisoquinoline sulfur trioxide complex with a substituted or unsubstituted epoxide to form said organic catalyst.
  • the process of making the aforementioned catalyst comprises the steps of reacting a substituted or unsubstituted 3,4-dihydroisoquinoline with a material selected from the group consisting of sulfur trioxide, a material that provides sulfur trioxide and mixtures thereof, to form a substituted or unsubstituted 3,4- dihydroisoquinoline sulfur trioxide complex, and reacting such substituted or unsubstituted 3,4- dihydroisoquinoline sulfur trioxide complex with a substituted or unsubstituted epoxide to form said organic catalyst.
  • the aromatic ring of the 3,4-dihydroisoquinoline does not appear to sulfonate to an extent that would limit the yield of catalyst.
  • the process of making the aforementioned catalyst comprises the step of reacting a substituted or unsubstituted 3,4-dihydroisoquinoline with a substituted or unsubstituted epoxide sulfur trioxide complex to form said organic catalyst.
  • the process of making the aforementioned catalyst comprises the steps of reacting a substituted or unsubstituted epoxide with a material selected from the group consisting of sulfur trioxide, a material that provides sulfur trioxide and mixtures thereof, to form a substituted or unsubstituted epoxide sulfur trioxide complex, and reacting such substituted or unsubstituted epoxide sulfur trioxide complex with a substituted or unsubstituted 3,4-dihydroisoquinoline to form said organic catalyst.
  • the oxaziridinium ring containing version of the aforementioned catalyst may be produced by contacting an iminium ring containing version of said catalyst with an oxygen transfer agent such as a peroxycarboxylic acid or a peroxymonosulfuricacid. Such species can be formed in situ and used without purification.
  • reaction temperatures of from about 0°C to about 150°C, or from about 0°C to about 125°C
  • reaction pressures of from about 0.1 to about 100 atmospheres, from about 0.3 atmospheres to about 10 atmospheres or from about 1 atmosphere to about 10 atmospheres
  • reaction times of 0.1 hours to about 96 hours, from about 1 hour to about 72 hours, or from about 1 hour to about 24 hours.
  • the reaction may also be run under an inert atmosphere or otherwise anhydrous conditions including, when a solvent is employed, the use of an anhydrous solvent.
  • the initial reaction mixture typically comprises from about 0.5 weight % to about 70 weight %, from about 5 weight % to about 70 weight %, or from about 10 weight % to about 50 weight % of such material.
  • Suitable substituted or unsubstituted 3,4-dihydroisoquinolines include 3,4-dihydro-6,7-dimethoxy-isoquinoline; 3,4- dihydro-3-methyl-isoquinoline; and l-methyl-3,4 dihydroisoquinoline, all available from Acros Organics Janssens Parmaceuticalaan 3AGeel, 2440 Belgium.
  • l-Benzyl-3,4-dihydro-isoquinoline available from City Chemical LLC, 139 Allings Crossing Road, West Haven, CT, 06516 USA.
  • 3,4-dihydro-3,3-dimethyl-isoquinoline available from MicroChemistry Ltd. Shosse Entusiastov 56 Moscow, 111123 Russia.
  • the initial reaction mixture typically comprises from about 0.5 weight % to about 70 weight %, from about 5 weight % to about 70 weight %, or from about 10 weight % to about 50 weight % of such material.
  • Suitable substituted or unsubstituted epoxides include but are not limited to epoxides such as 2-ethylhexyl glycidyl ether; 1,2-epoxypropane; 2,2-dimethyl-oxirane; 2-methyl-oxiranecarboxylic acid, methyl ester; (2R,3R)-diphenyl-oxirane; (2S,3S)-2-methyl-3- phenyl oxirane; and 3-ethenyl-7-oxabicyclo[4.1.0]heptane, all available from Aldrich, P.O. Box 2060, Milwaukee, WI 53201, USA.
  • epoxides such as 2-ethylhexyl glycidyl ether; 1,2-epoxypropane; 2,2-dimethyl-oxirane; 2-methyl-oxiranecarboxylic acid, methyl ester; (2R,3R)-diphenyl-oxirane; (2S,3S)-2
  • epoxides include, 1,2-Epoxydodecane; 1 ,2-epoxyoctane; 2-ethyl-2-methyl-oxirane; 6,6-dimethyl-spiro[bicyclo[3.1.1 ]heptane-2,2'- oxirane]; 3-methyl-oxiranecarboxylic acid, ethyl ester; and 3,6-Dioxabicyclo[3.1.0]hexane, all available from Acros Organics, Janssens Parmaceuticalaan, 3A Geel, 2440 Belgium; 2-Methyl-2- phenyl-Oxirane, available from TCI America, 9211 N.
  • the initial reaction mixture typically comprises from about 0.5 weight % to about 70 weight %, from about 5 weight % to about 70 weight %, or from about 10 weight % to about 50 weight % of such material.
  • Suitable materials include sulfur trioxide, and sulfur trioxide complexes such as sulfur trioxide trimethylamine, sulfur trioxide dioxane, sulfur trioxide pyridine, sulfur trioxide N,N- dimethylformamide, sulfur trioxide sulfolane, sulfur trioxide tetrahydrofuran, sulfur trioxide diethylether, and sulfur trioxide 3,4-dyhydroisoquinoline.
  • Suitable sulfur trioxide complexes and sulfur trioxide can be purchased from Aldrich, P.O. Box 2060, Milwaukee, WI 53201, USA or prepared according to the teachings of this specification.
  • the balance of any reaction mixture is typically solvent.
  • the initial reaction mixture typically comprises up to 99 weight % solvent, from about 10 weight % to about 90 weight % solvent, or from about 20 weight % to about 80 weight % solvent.
  • Suitable solvents include aprotic, polar and apolar solvents such as acetonitile, dioxane, tertbutyl methylether, tetrahydrofuran, N,N-dimethylformamide, sulfolane, chlorobenzene, toluene, 1,2 dichloroethane, methylene chloride, chloroform, diethyl ether, hexanes, pentanes, benzene and xylenes.
  • Suitable solvents can be purchased from Aldrich, P.O. Box 2060, Milwaukee, WI 53201, USA.
  • Organic catalysts produced according to the process described herein may be advantageously employed in cleaning and/or bleaching applications for example, in laundry applications, hard surface cleaning, automatic dishwashing applications, as well as cosmetic applications such as dentures, teeth, hair and skin.
  • the organic catalysts of the present invention may also be employed in a cleaning additive product.
  • a cleaning additive product including the organic catalysts of the present invention is ideally suited for inclusion in a wash process when additional bleaching effectiveness is desired. Such instances may include, but are not limited to, low temperature solution cleaning application.
  • the additive product may be, in its simplest form, the organic catalyst.
  • the additive could be packaged in dosage form for addition to a cleaning process where a source of peroxygen is employed and increased bleaching effectiveness is desired.
  • Such single dosage form may comprise a pill, tablet, gelcap or other single dosage unit such as pre-measured powders or liquids.
  • a filler or carrier material may be included to increase the volume of such composition. Suitable filler or carrier materials include, but are not limited to, various salts of sulfate, carbonate and silicate as well as talc, clay and the like. Filler or carrier materials for liquid compositions may be water or low molecular weight primary and secondary alcohols including polyols and diols.
  • Such alcohols include, but are not limited to, methanol, ethanol, propanol and isopropanol.
  • the compositions may contain from about 5% to about 90% of such materials.
  • Acidic fillers can be used to reduce pH.
  • the cleaning additive may include activated peroxygen source defined below or the adjunct ingredients as fully defined below. Cleaning compositions and cleaning additives require a catalytically effective amount of organic catalyst. The required level of such catalyst may be achieved by the addition of one or more species of the organic catalyst produced according to the process disclosed herein.
  • compositions and cleaning processes herein can be adjusted to provide on the order of at least 0.001 ppm of organic catalyst in the washing medium, and will preferably provide from about 0.001 ppm to about 500 ppm, more preferably from about 0.005 ppm to about 150 ppm, and most preferably from about 0.05 ppm to about 50 ppm, of the organic catalyst in the wash liquor.
  • typical compositions herein will comprise from about 0.0002% to about 5%, more preferably from about 0.001% to about 1.5%, of organic catalyst, by weight of the cleaning compositions.
  • the organic catalyst When said organic catalyst is employed in a granular composition, it may be desirable for the organic catalyst to be in the form of an encapsulated particle that protects the organic catalyst from moisture and/or other components of the granular composition during storage.
  • encapsulation is also a means of controlling the availability of the organic catalyst during the cleaning process and may enhance the bleaching performance of the organic catalyst.
  • the organic catalyst can be encapsulated with any encapsulating material known in the art.
  • the encapsulating material typically encapsulates at least part, preferably all, of the Applicants' organic catalyst.
  • the encapsulating material is water-soluble and/or water- dispersible.
  • the encapsulating material may have a glass transition temperature (Tg) of 0°C or higher.
  • cleaning compositions must comprise an activated peroxygen source.
  • Suitable ratios of moles of organic catalyst to moles of activated peroxygen source include but are not limited to from about 1:1 to about 1:1000.
  • Suitable activated peroxygen sources include, but are not limited to, preformed peracids, a hydrogen peroxide source in combination with a bleach activator, or a mixture thereof.
  • Suitable preformed peracids include, but are not limited to, compounds selected from the group consisting of percarboxylic acids and salts, percarbonic acids and salts, perimidic acids and salts, peroxymonosulfuric acids and salts, and mixtures thereof.
  • Suitable sources of hydrogen peroxide include, but are not limited to, compounds selected from the group consisting of perborate compounds, percarbonate compounds, perphosphate compounds and mixtures thereof.
  • Suitable bleach activators include, but are not limited to, tetraacetyl ethylene diamine (TAED), benzoylcaprolactam (BzCL), 4-nitrobenzoylcaprolactam, 3-chlorobenzoylcaprolactam, benzoyloxybenzenesulphonate (BOBS), nonanoyloxybenzenesulphonate (NOBS), phenyl benzoate (PhBz), decanoyloxybenzenesulphonate (Cio-OBS), benzoylvalerolactam (BZVL), octanoyloxybenzenesulphonate (C 8 -OBS), perhydrolyzable esters, perhydrolyzable imides and mixtures thereof
  • hydrogen peroxide sources will typically be at levels of from about 1%, preferably from about 5% to about 30%, preferably to about 20% by weight of the composition.
  • peracids or bleach activators will typically comprise from about 0.1%, preferably from about 0.5% to about 60%, more preferably from about 0.5% to about 40% by weight of the bleaching composition.
  • suitable types and levels of activated peroxygen sources are found in U.S. Patent Nos. 5,576,282, 6,306,812 Bl and 6,326,348 Bl that are incorporated by reference.
  • the cleaning compositions herein will preferably be formulated such that, during use in aqueous cleaning operations, the wash water will have a pH of between about 6.5 and about 11, preferably between about 7.5 and 10.5.
  • Liquid dishwashing product formulations preferably have a pH between about 6.8 and about 9.0.
  • Laundry products are typically at pH 9-11. Techniques for controlling pH at recommended usage levels include the use of buffers, alkalis, acids, etc., and are well known to those skilled in the art.
  • adjuncts While not essential for the purposes of the present invention, the non-limiting list of adjuncts illustrated hereinafter are suitable for use in the instant cleaning compositions and may be desirably incorporated in preferred embodiments of the invention, for example to assist or enhance cleaning performance, for treatment of the substrate to be cleaned, or to modify the aesthetics of the cleaning composition as is the case with perfumes, colorants, dyes or the like.
  • the precise nature of these additional components, and levels of incorporation thereof, will depend on the physical form of the composition and the nature of the cleaning operation for which it is to be used.
  • Suitable adjunct materials include, but are not limited to, surfactants, builders, chelating agents, dye transfer inhibiting agents, dispersants, enzymes, and enzyme stabilizers, catalytic metal complexes, polymeric dispersing agents, clay soil removal/anti-redeposition agents, brighteners, suds suppressors, dyes, perfumes, structure elasticizing agents, fabric softeners, carriers, hydrotropes, processing aids and/or pigments.
  • surfactants builders, chelating agents, dye transfer inhibiting agents, dispersants, enzymes, and enzyme stabilizers, catalytic metal complexes, polymeric dispersing agents, clay soil removal/anti-redeposition agents, brighteners, suds suppressors, dyes, perfumes, structure elasticizing agents, fabric softeners, carriers, hydrotropes, processing aids and/or pigments.
  • the cleaning compositions according to the present invention comprise a surfactant or surfactant system wherein the surfactant can be selected from nonionic and/or anionic and/or cationic surfactants and/or ampholytic and/or zwitterionic and/or semi-polar nonionic surfactants.
  • the surfactant is typically present at a level of from about 0.1%, preferably about 1%, more preferably about 5% by weight of the cleaning compositions to about 99.9%, preferably about 80%, more preferably about 35%, most preferably about 30% by weight of the cleaning compositions.
  • Builders - The cleaning compositions of the present invention preferably comprise one or more detergent builders or builder systems.
  • compositions will typically comprise at least about 1% builder, preferably from about 5%, more preferably from about 10% to about 80%, preferably to about 50%, more preferably to about 30% by weight, of detergent builder.
  • Builders include, but are not limited to, the alkali metal, ammonium and alkanolammonium salts of polyphosphates, alkali metal silicates, alkaline earth and alkali metal carbonates, aluminosilicate builders polycarboxylate compounds, ether hydroxypolycarboxylates, copolymers of maleic anhydride with ethylene or vinyl methyl ether, 1, 3, 5-trihydroxy benzene- 2, 4, 6-trisulphonic acid, and carboxymethyloxysuccinic acid, the various alkali metal, ammonium and substituted ammonium salts of polyacetic acids such as ethylenediamine tetraacetic acid and nitrilotriacetic acid, as well as polycarboxylates such as mellitic acid, succin
  • the cleaning compositions herein may also optionally contain one or more copper, iron and/or manganese chelating agents. If utilized, these chelating agents will generally comprise from about 0.1% by weight of the cleaning compositions herein to about 15%, more preferably 3.0% by weight of the cleaning compositions herein.
  • Dye Transfer Inhibiting Agents The cleaning compositions of the present invention may also include one or more dye transfer inhibiting agents.
  • Suitable polymeric dye transfer inhibiting agents include, but are not limited to, polyvinylpyrrolidone polymers, polyamine N-oxide polymers, copolymers of N-vinylpyrrolidone and N-vinylimidazole, polyvinyloxazolidones and polyvinylimidazoles or mixtures thereof.
  • the dye transfer inhibiting agents are present at levels from about 0.0001%, more preferably about 0.01%, most preferably about 0.05% by weight of the cleaning compositions to about 10%, more preferably about 2%, most preferably about 1% by weight of the cleaning compositions.
  • Dispersants The cleaning compositions of the present invention can also contain dispersants.
  • Suitable water-soluble organic materials are the homo- or co-polymeric acids or their salts, in which the polycarboxylic acid comprises at least two carboxyl radicals separated from each other by not more than two carbon atoms.
  • Enzymes - The cleaning compositions can comprise one or more detergent enzymes which provide cleaning performance and/or fabric care benefits.
  • suitable enzymes include, but are not limited to, hemicellulases, peroxidases, proteases, cellulases, xylanases, lipases, phospholipases, esterases, cutinases, pectinases, keratanases, reductases, oxidases, phenoloxidases, lipoxygenases, ligninases, pullulanases, tannases, pentosanases, malanases, ⁇ - glucanases, arabinosidases, hyaluronidase, chondroitinase, laccase, and known amylases, or mixtures thereof.
  • a preferred combination is a cleaning composition having a cocktail of conventional applicable enzymes like protease, lipase, cutinase and/or cellulase in conjunction with amylase.
  • Enzyme Stabilizers - Enzymes for use in detergents can be stabilized by various techniques.
  • the enzymes employed herein can be stabilized by the presence of water-soluble sources of calcium and/or magnesium ions in the finished compositions that provide such ions to the enzymes.
  • Catalytic Metal Complexes - Applicants' cleaning compositions may include catalytic metal complexes.
  • One type of metal-containing bleach catalyst is a catalyst system comprising a transition metal cation of defined bleach catalytic activity, such as copper, iron, titanium, ruthenium, tungsten, molybdenum, or manganese cations, an auxiliary metal cation having little or no bleach catalytic activity, such as zinc or aluminum cations, and a sequestrate having defined stability constants for the catalytic and auxiliary metal cations, particularly ethylenediaminetetraacetic acid, ethylenediaminetetra (methylenephosphonic acid) and water- soluble salts thereof.
  • a transition metal cation of defined bleach catalytic activity such as copper, iron, titanium, ruthenium, tungsten, molybdenum, or manganese cations
  • an auxiliary metal cation having little or no bleach catalytic activity such as zinc or aluminum cations
  • a sequestrate having defined stability constants for the catalytic and auxiliary metal cations, particularly ethylenediaminetetra
  • compositions herein can be catalyzed by means of a manganese compound.
  • a manganese compound Such compounds and levels of use are well known in the art and include, for example, the manganese-based catalysts disclosed in U.S. 5,576,282 Miracle et al.
  • Cobalt bleach catalysts useful herein are known, and are described, for example, in U.S. 5,597,936 Perkins et al, issued January 28, 1997; U.S. 5,595,967 Miracle et al., January 21, 1997.
  • Such cobalt catalysts are readily prepared by known procedures, such as taught for example in U.S. 5,597,936, and U.S. 5,595,967.
  • compositions herein may also suitably include a transition metal complex of a macropolycyclic rigid ligand - abreviated as "MRL".
  • MRL macropolycyclic rigid ligand - abreviated as "MRL”.
  • the compositions and cleaning processes herein can be adjusted to provide on the order of at least one part per hundred million of the active MRL species in the aqueous washing medium, and will preferably provide from about 0.005 ppm to about 25 ppm, more preferably from about 0.05 ppm to about 10 ppm, and most preferably from about 0.1 ppm to about 5 ppm, of the MRL in the wash liquor.
  • Preferred transition-metals in the instant transition-metal bleach catalyst include manganese, iron and cliromium.
  • Preferred MRL's herein are a special type of ultra-rigid ligand that is cross-bridged such as 5,12-diethyl-l,5,8,12-tetraazabicyclo[6.6.2]hexadecane.
  • Suitable transition metal MRLs are readily prepared by known procedures, such as taught for example in WO 00/332601, and U.S. 6,225,464.
  • the cleaning compositions of the present invention can be formulated into any suitable form and prepared by any process chosen by the formulator, non-limiting examples of which are described in U.S. 5,879,584 Bianchetti et al., issued March 9, 1999; U.S. 5,691,297 Nassano et al., issued November 11, 1997; U.S. 5,574,005 Welch et al., issued November 12, 1996; U.S. 5,569,645 Dinniwell et al., issued October 29, 1996; U.S. 5,565,422 Del Greco et al., issued October 15, 1996; U.S.
  • the cleaning and/or bleaching compositions employing said organic catalyst can be used to bleach and/or clean a situs inter alia a surface or fabric.
  • Such method includes the steps of contacting an embodiment of Applicants' cleaning composition, in neat form or diluted in a wash liquor, with at least a portion of a surface or fabric then rinsing such surface or fabric.
  • the surface or fabric is subjected to a washing step prior to the aforementioned rinsing step.
  • washing includes but is not limited to, scrubbing, and mechanical agitation.
  • the cleaning and/or bleaching compositions of the present invention are ideally suited for use in laundry applications wherein a fabric is contacted with a cleaning laundry solution comprising at least one embodiment of Applicants cleaning composition, cleaning additive or mixture thereof.
  • the fabric may comprise most any fabric capable of being laundered in normal consumer use conditions.
  • the solution preferably has a pH of from about 8 to about 10.5.
  • the compositions are preferably employed at concentrations of from about 500 ppm to about 15,000 ppm in solution.
  • the water temperatures preferably range from about 5 °C to about 90 °C.
  • the water to fabric ratio is preferably from about 1:1 to about 30:1.
  • Synthesis routes for Examples 1-16 are depicted herein. In such routes all structures are general structures and the moieties Ri, R 2 , R 3 , 3 ', Rt Rr, Rs, Re, R7 and Rs may be any suitable organic or inorganic moiety. While the synthetic pathways detailed herein employ specific synthetic transformations, as will be appreciated by one skilled in the art, other suitable synthetic transformations may be employed.
  • 3,4-dihydroisoquinoline (1) may be obtained from benzyl nitrile (6) or (7), phenethylamine (8) and formamide (9) using the synthetic pathways detailed above.
  • the moieties R 3 , R 3 -, R t R 4 ', R 5 , Re, R 7 and R 8 may be any suitable organic or inorganic moiety.
  • Raw materials required for the aforementioned syntheses are generally commercially available. The following materials can be obtained from Aldrich, P.O.
  • toluene 250 ml
  • To the addition funnel is added formic acid (46 gm., 1 mol).
  • the l-chloro-3-(2-propyl-heptyloxy)-propan-2-ol (5.0 gm., 0.020 moles) is dissolved in tetrahydrofuran (50 mL) and stirred at RT under an argon atmosphere.
  • potassium tert-butoxide (2.52 gm., 0.022 moles) and the suspension is stirred at RT for 18 hours.
  • 3,4-dihydroisoquinoline ( 1) may be converted to its sulfur trioxide 3,4-dihydroisoquinoline complex ( 2) via contacting 3,4-dihydroisoquinoline ( 1) with a source of SO 3 , followed by contacting the sulfur trioxide 3,4-dihydroisoquinoline complex (2) with an appropriate glycidal ether (3) to give organic catalyst (5).
  • an appropriate glycidal ether (3) may be converted to its sulfur trioxide glycidal ether complex (4) via contacting the appropriate glycidal ether (3) with a source of SO 3 , followed by contacting the sulfur trioxide glycidal ether complex(4) with 3,4-dihydroisoquinoline (1) to give organic catalyst (5).
  • Organic catalyst (5) may also be prepared by contacting simultaneously 3,4-dihydroisoquinoline (1), glycidal ether (3), and a source of sulfur trioxide in a single operation.
  • Raw materials required for the aforementioned syntheses are generally commercially available. The following materials can be obtained from Aldrich, P.O.
  • 6,7-Dimethoxy-3,4- dihydroisoquinoline hydrochloride hydrate can be purchased form Fisher Scientific 1 Reagent Lane Fair Lawn, NJ, 07410 USA.
  • Glycidal ethers such as (2-ethylhexyloxy)oxiran-2-ylmethane can be acquired through the Raschig Corporation, 129 South Scoville Avenue, Oak Park IL, 60302, U.S.A, under the product name EHGE.
  • Example 8 Preparation of Sulfuric acid mono- [2-(3.4-dihvdro-isoquinolin-2-yl I -(2-ethyl- hexyloxymethylVethyll ester, internal salt via synthesis route (1) to (2) to (5)
  • the methylene chloride is removed via Dean Stark Trap and once removed an internal reaction temperature of 75-80°C is obtained, upon which the reaction turns clear/amber.
  • the reaction is stirred at 75-80°C for 72 hours.
  • Example 10 Preparation of Sulfuric acid mono- r 2-f3,4-dihydro-isoquinolin-2-yl)-l- (2,2,3 ,3,4,4,5,5,6,6,7.7-dodecafluroheptyloxymethyl)-ethvn ester, internal salt
  • glycidyl 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluoroheptyl ether (3) (12.8 gm, 0.038 mol) and acetonitrile (50 ml).
  • the solids (2) are placed in a flame dried 250 ml round bottomed flask equipped with an argon inlet, condenser, magnetic stir bar, and heating bath, and suspended in acetonitrile (50 ml). To the suspension is added glycidyl 4- nonylphenyl ether (3) (10.5 gm, 0.038 mol) and the reaction is brought to reflux. Reaction is stirred at reflux for 72 hours.
  • Example 13 Preparation of Commercial Quantities Of Catalyst In a Stirred Tank Reactor
  • a glycidal ether is contacted with a source of SO 3 , either neat or with an appropriate aprotic solvent, for less than about 240 minutes, at a temperature of from about 0 °C to about 80 °C, and a pressure of about 1 atmosphere followed by addition of a 3,4-dihydroisoquinoline and contacting the resulting reaction mixture for less than about 96 hours, at a temperature of from about 50 °C to about 150 °C, and a pressure of about 1 atmosphere.
  • Such process is conducted in a stirred tank reactor and results in the formation of an organic catalyst.
  • Example 14 Preparation of Commercial Quantities Of Catalyst In a Stirred Tank Reactor
  • a 3,4-dihydroisoquinoline is contacted with a source of SO 3 , either neat or with an appropriate aprotic solvent, for less than about 240 minutes, at a temperature of from about 0 °C to about 80 °C, and a pressure of about 1 atmosphere followed by addition of a glycidal ether and contacting the resulting reaction mixture for less than about 96 hours, at a temperature of from about 50 °C to about 150 °C, and a pressure of about 1 atmosphere.
  • Such process is conducted in a stirred tank reactor and results in the formation of organic catalyst.
  • Example 15 Preparation of Commercial Quantities Of Catalyst In a Stirred Tank Reactor A 3,4-dihydroisoquinoline, a source of SO 3 , and a glycidal ether, either neat or with an appropriate aprotic solvent, for less than about 96 hours, at a temperature of from about 50 °C to about 150 °C, and a pressure of about 1 atmosphere. Such process is conducted in a stirred tank reactor and results in the formation of organic catalyst.
  • Example 16 Method of preparing a particle comprising the Applicants' organic catalyst lOg of the Applicants' organic catalyst according to any of Examples 8-12 above is mixed thoroughly with 80 gm of sodium sulfate, 10 gm of sodium lauryl sulfonate, and 10 gm of water at 70°-90° C, to form a paste. The paste is allowed to dry to a brittle solid, and the solid is ground into a fine powder, thereby producing the desired carrier particulates.
  • Example 17 Method of preparing a granular detergent comprising the Applicants' organic catalyst
  • Granular detergents comprising 0.002% to 5% of Applicants' organic catalyst, are made by dusting fine particulates (particulates having a mean particle size of less than about 100 um) comprising Applicants' catalyst on to a detergent mix during the detergent making process, and/or by combining a carrier particle comprising Applicants' catalyst with said detergent mix during the detergent making process.
  • Such finished detergents are found to contain a uniform distribution of Applicants' organic catalyst wherein the relative standard deviation is less than 20% per 30 gram sample.

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Abstract

Cette invention porte sur une préparation de sulfates zwitterioniques de 3, 4-dihydroisoquinoline substituée ou non substituée.
PCT/US2004/036987 2003-11-06 2004-11-04 Procede de production de zwitterions de dihydroisoquinoline Ceased WO2005047264A1 (fr)

Priority Applications (4)

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JP2006538520A JP2007513071A (ja) 2003-11-06 2004-11-04 ジヒドロイソキノリン双性イオンを製造するための有機触媒の製造方法
CA002544547A CA2544547A1 (fr) 2003-11-06 2004-11-04 Procede de production de zwitterions de dihydroisoquinoline
EP04800814A EP1680404A1 (fr) 2003-11-06 2004-11-04 Procede de production de zwitterions de dihydroisoquinoline
MXPA06005028A MXPA06005028A (es) 2003-11-06 2004-11-04 Proceso para producir zwitteriones de dihidroisoquinolina.

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US51794703P 2003-11-06 2003-11-06
US60/517,947 2003-11-06
US51944303P 2003-11-12 2003-11-12
US60/519,443 2003-11-12
US53110003P 2003-12-19 2003-12-19
US60/531,100 2003-12-19

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